A boisterous port city on the surface, this urban capital of Crete hides millennia of history beneath its modern trappings. In Heraklion, scooters zip past Minoan and medieval relics such as the seaside Koules Fortress, while Turkish fountains bubble up in the shadow of apartment blocks.

Once known for smog, traffic and tacky architecture, Athens is a city reformed thanks to fortunes brought by the 2004 Summer Olympics. Spotless parks and streets, an ultra-modern metro, new motorways, an accessible airport and all signs in perfect English make the city easily negotiable. Meriting more than a stopover en route to the islands, sophisticated Athens sites include many pillars of Western history, from the Acropolis to the Temple of Olympian Zeus, as well as treasures in the National Archaeological Museum.

Lying in south central Turkey, the moonscaped region of Cappadocia, southeast of Ankara, is most famous for unique geological features called fairy chimneys. The large, cone-like formations were created over time by erosion of the relatively soft volcanic ash around them. Past cultures have dug into them to create dwellings, castles (like Uchisar) and even entire underground cities like Kaymakli and Derinkuyu, used as hiding places by early Christians. Nearby Kayseri is the gateway to the area.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?

Looking out over the city of St. John's, you may be reminded of a mini San Francisco (minus the cable cars). St. John's provides the ideal balance between nature and nightlife, from the East Coast Trail and its stunning scenery to the colourful entertainment district along George Street. Although it's the largest city in Newfoundland, the vibe is still very small-town. You'll feel welcome in the City of Legends!

"For simple beauty, Cape Breton outrivals them all." So said Alexander Graham Bell of the island he adopted as his home. Rich with Celtic, Mi'kmaq and Acadian heritage, Cape Breton is a delight for history buffs, music lovers and explorers of nature. Immerse yourself in 18th-century life at the Fortress of Louisbourg, explore the winding roads and Atlantic vistas of the Cabot Trail, and seek out a local Ceilidh for a lively and rousing experience.